George Trow’s Within the Context of No Context was a brilliant, scary vision of a cultural end-time. Then, having described it, he lived it, spiraling into madness.

In the late afternoon in the late forties, young George William Swift Trow Jr. would stand in front of the window of his parents’ living room in Cos Cob, Connecticut, watching and waiting. He did not watch television, of course, he watched the street, until he saw the form of his father, crowned by a fedora. They would wave at each other, and then his father, a city editor of the New York Post, would come in, put down his stack of newspapers, hug his wife, and put his fedora on his son’s head. Everyone knew who was an adult and who was a child in this kingdom; everyone knew the rituals. Another: From the time Trow was 7 years old, his father made sure that he read (at least) the Herald Tribune and “knew how to follow the story over from page 1 to page 32, folding the newspaper while existing in a small confined space,” as in the subway that Trow would one day take to his own job in New York City.

And in fact Trow did wear a fedora for a while—to the great amusement of his colleagues—when he was a young writer at William Shawn’s New Yorker. “This is the sixties, so to wear a fedora is some kind of a big statement,” says Jonathan Schell, who, like Trow, graduated from Harvard in 1965 and was swiftly hired by Shawn. “Since Kennedy didn’t wear one, it was like a high wind blew through the country and took off all the hats. For George, the hat had something to do with being an adult, but some kind of mockery of being an adult. The fedora was like a flag of our fathers: No one else wore a fedora except William Shawn.”

There was much of Trow in that hat: his Shawn worship, his interest in considered and dapper self-presentation (something he shared with his friend Diana Vreeland), the fact that his father and his father’s world and, most important, the loss of his father’s world were never far from Trow’s mind. “I know he was sort of engaged in a conversation with his dad in his thoughts, and that he was very, very influenced by his dad’s view of the world—either to argue for it or against it,” says Ian Frazier, Trow’s New Yorker colleague and close friend for many years.

Nothing was ever just what it was to Trow. “He was always thinking behind his own back,” Alison Rose wrote in her memoir, Better Than Sane (the title is taken from a comment Trow made to Rose when they were New Yorker colleagues in the eighties and formed a little club he called “Insane Anonymous”). Trow made a life out of deconstructing “Mainstream American Cultural Artifacts,” as he put it, searching for meaning in Eisenhower’s Rolodex, the layout of Life magazine, his own hat. “Irony has seeped into the felt of any fedora hat I have ever owned—not out of any wish of mine but out of necessity. A fedora hat worn by me without the necessary protective irony would eat through my head and kill me,” Trow wrote in his famous essay “Within the Context of No Context,”first published in its entirety in The New Yorker in 1980 and later republished as a book. “It turns out that while I am at home in many strange places, I am not free even to visit the territory I was expected to inhabit effortlessly. To wear a fedora, I must first torture it out of shape.”

“Within the Context of No Context” is a tale of the fall. It divided the world into a time when the world was whole, made sense, and after, when life was still possible but the culture had been ruined. Many factors were to blame, but perhaps the most poisonous force was television—certainly the most representative of all that had brought the kingdom of history and learning and liberal arts and newspapers and fedoras to its knees. The book made sense of people’s sense of loss, especially that of well-educated young people who by other measures might be said to have lost nothing. Stylistically, it was remarkable, a hypnotic procession of aphorisms that was probably the most extreme work of nonfiction The New Yorker hasever published; some readers questioned the sanity of a man who could produce such a shriek.

Trow’s colleagues took note of his increasing eccentricity, but The New Yorker in that period forgave, even rewarded, a temperament like Trow’s. It was a safe place—for Trow, possibly the last one. Shawn was fired in 1987. With Tina Brown’s arrival in 1992, the barbarians had sacked the castle.